One of my core strategies as a VC has always been to aggressively facilitate conversations between the entrepreneurs that I work with. Over the last 13 years, this has paid off in numerous ways, endless times. A while ago I realized that, in addition to being a lot of fun (usually for all involved), it was a way for me to learn an incredible amount by just watching where the entrepreneurs took the conversations.

I’ve always been fascinated by “CTO’s talking.” Whenever two or more CTO’s are in the room, I want to be part of the conversation. Some of that may have come from my pre-VC life, but I think it’s because there is rarely any gloss on the thought processes as my CTO friends dig deep into whatever topic they are discussing.

It’s even more fun when the CTO turned CEO hangs out with his CTO and talks with another CTO (did you follow that)? Todd Vernon and Tim Wolters two great, experienced CTO’s in Boulder. Todd is now CEO of Lijit (after being the CTO and co-founder of Raindance) and partners with the founder / CTO – Stan James. Tim is the co-founder / CTO of Collective Intellect (after being the co-founder / CTO of Dante Group which webMethods acquired in 2003). Yesterday, Todd, Tim, and Stan spent some time together and “the long tail of vertical search” popped out. Lots of people have been working on “vertical search” – but not many (as far as I can tell) are really focused on the second order effects of vertical search, which is where I think the real money is. Yeah – that’s an abstract statement – but that’s the fun of it.

Todd and Stan’s business (Lijit) is banging away trying to figure this out, as is Tim’s business (Collective Intellect). I’m an investor in both of them and am fascinated and delighted with the evolution of their ideas and products. The are working on fundamentally hard stuff – both conceptually and functionally – and when they deliver it in a way my dad will understand and use it – they’ll be on to something really big.